Category: 68774-77-6

Adding a certain compound to certain chemical reactions, such as: 68774-77-6, name is 8-Chloro[1,2,4]triazolo[4,3-a]pyrazine, belongs to pyrazines compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 68774-77-6, HPLC of Formula: C5H3ClN4

A mixture of crude 4-methylbenzyl 4-(aminomethyl)-3,3-difluoropiperidine-1-carboxylate (600mg, 2.0 mmol), 8-chloro-[1,2,4]triazolo[4,3-a]pyrazine (360 mg, 2.0 mmol) and DIPEA (0.76 mL, 4.0 mmol) in butyl alcohol (10 mL) was heated at 130 C overnight. The mixture was allowed to cool to room temperature and concentrated under reduced pressure. The concentrate was purified by column chromatography over silica gel (100% ethyl acetate) to afford the title compound as a light gray powder (150 mg, 18%). MS (ESI) calcd for C20H22F2N602: 416.2; found: 417.3 [M+H]. 1H NMR (400MHz, CD3OD) 6 9.16 (s, 1H), 7.77 (d, J = 4.8 Hz, 1H), 7.29 (d, J = 4.8 Hz, 1H), 7.24 (d, J = 8.0 Hz, 2H), 7.17 (d, J = 8.0 Hz, 2H), 5.09 (s, 2H), 4.33 (br s, 1H), 4.19-4.15 (m, 1H), 4.05-3.95 (m, 1H), 3.72-3.58 (m, 1H), 3.25-2.90 (m, 2H), 2.67-2.51 (m,1H), 2.33 (s, 3H), 1.99-1.93 (m, 1H), 1.62-1.52 (m, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 8-Chloro[1,2,4]triazolo[4,3-a]pyrazine, and friends who are interested can also refer to it.

Reference:
Patent; RUGEN HOLDINGS (CAYMAN) LIMITED; SHAPIRO, Gideon; (246 pag.)WO2016/196513; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 68774-77-6, name is 8-Chloro[1,2,4]triazolo[4,3-a]pyrazine, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 8-Chloro[1,2,4]triazolo[4,3-a]pyrazine

General procedure: A mixture of chloro compound (50 mg) and amine derivative (2 equiv.) in PEG 400 (2 mL) wasstirred at 120 C for 5 min. After completion the reaction was then cooled to room temperature. DCM and water were added and the phases were separated. The aqueous phase was extracted withDCM and the organic phase was dried and filtered. The removal of solvent gave the product as solid.

According to the analysis of related databases, 68774-77-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Campos, Joana F.; Loubidi, Mohammed; Scherrmann, Marie-Christine; Berteina-Raboin, Sabine; Molecules; vol. 23; 3; (2018);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 68774-77-6, A common heterocyclic compound, 68774-77-6, name is 8-Chloro[1,2,4]triazolo[4,3-a]pyrazine, molecular formula is C5H3ClN4, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a solution of the product of Example 365A (70 mg, 0.153 mmol) in N,N- dimethylformamide (1 mL) was added 8-chloro-[1,2,4]triazolo[4,3-a]pyrazine (35.5 mg, 0.230 mmol) and N,N-diisopropylethylamine (0.080 mL, 0.460 mmol). The reaction mixture was stirred for 4 days at 70 C and then was purified by preparative HPLC [Waters XBridge C18 5 mum OBD column, 30 × 100 mm, flow rate 40 mL/minute, 5-100% gradient of acetonitrile in buffer (0.1 % trifluoroacetic acid)] to give the title compound (15 mg, 0.026 mmol, 17% yield). 1H NMR (400 MHz, DMSO-d6) delta ppm 9.17 (s, 1H), 7.75 (d, J = 4.8 Hz, 1H), 7.54 (s, 1H), 7.45 (t, J = 8.9 Hz, 1H), 7.23 (d, J = 4.9 Hz, 1H), 7.00 (dd, J = 11.4, 2.9 Hz, 2H), 6.79 (ddd, J = 9.0, 2.9, 1.2 Hz, 1H), 4.42 (s, 2H), 4.17 – 4.14 (m, 2H), 2.64 – 2.50 (m, 1H), 2.35 (ddd, J = 12.8, 9.4, 2.9 Hz, 1H), 2.27 – 2.13 (m, 1H), 2.04 – 1.77 (m, 8H); 19F NMR (376 MHz, DMSO-d6) delta ppm -75.00, -114.17; MS (ESI+) m/z 461 (M+H)+ .

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; CALICO LIFE SCIENCES; ABBVIE, INC.; SIDRAUSKI, Carmela; PLIUSCHEV, Marina; FROST, Jennifer, M.; BLACK, Lawrence, A.; XU, Xiangdong; SWEIS, Ramzi, Farah; SHI, Lei; ZHANG, Qinwei, I.; TONG, Yunsong; HUTCHINS, Charles, W.; CHUNG, Seungwon; DART, Michael, J.; (661 pag.)WO2017/193063; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 68774-77-6, name is 8-Chloro[1,2,4]triazolo[4,3-a]pyrazine, A new synthetic method of this compound is introduced below., Recommanded Product: 68774-77-6

Add p-aminophenol (0.78 g, 7.2 mmol) and potassium tert-butoxide (1.46 g, 13.0 mmol) to the flask, use tetrahydrofuran as a solvent, and stir under an ice bath for 1 h under the protection of nitrogen; intermediate c (1 g, 6.5 mmol) and potassium iodide (0.12 g, 0.72 mmol) were added to the flask, tetrahydrofuran was used as a solvent, and the temperature was raised to 80 C., and the p-aminophenol after the reaction was added thereto, and reacted under the protection of nitrogen. After the reaction is completed, suction filtration is performed. The filtrate is spin-evaporated. After evaporation to dryness, a small amount of NaOH aqueous solution is added to sonicate, solids are precipitated, suction-filtered, and the filter cake is dried to obtain 0.45 g of a gray solid with a yield of 30.6%.

The synthetic route of 68774-77-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangxi Science and Technology Normal University; Zhu Wufu; Zheng Pengwu; Xu Shan; Liu Xiaobo; Zhang Qian; Zhou Lingjia; Han Haoyun; Yu Li; Zhou Hualan; Qiu Yufeng; (25 pag.)CN110467616; (2019); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 68774-77-6, name is 8-Chloro[1,2,4]triazolo[4,3-a]pyrazine, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 8-Chloro[1,2,4]triazolo[4,3-a]pyrazine

Compound 49B (2.0 g, 13.0 mmol), platinum dioxide (1 g) and palladium on carbon (0.4 g) were added to methanol (100 mL).Hydrogenation at 50 psi for 14 hours, filtration,The organic solvent is dried under reduced pressure,Compound 49C was obtained as a brown solid product(1.4 g, yield 88%).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 68774-77-6.

Reference:
Patent; Jiangsu Xiansheng Pharmaceutical Co., Ltd.; Chen Huanming; Liang Bo; Zhao Zhongqiang; Cao Wenjie; Xu Wanmei; Li Qingsong; Wang Jianghuai; Zhang Peng; Jiang Zhaojian; Zhang Guiping; Gao Chunhua; Gong Hongju; Zuo Gaolei; (86 pag.)CN108250128; (2018); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 68774-77-6 as follows. Formula: C5H3ClN4

Example 22 (2R,3S)-3-([1,2,4]triazolo[4,3-a]pyrazin-8-ylamino)-1-((R)-6-bromo-2,2-spirocyclobutanechroman-4-ylamino)-4-phenylbutan-2-ol. To a solution of 8-chloro-[1,2,4]triazolo[4,3-a]pyrazine (0.032 g, 0.21 mmol) and sodium carbonate monohydrate (0.026 g, 0.21 mmol) in ethanol (2 mL) and dimethylformamide was added the chroman-amine (0.89 g, 0.21 mmol). The resulting mixture was stirred and heated at 60 C. for 17 h. The mixture was concentrated and the residue was dissolved in ethyl acetate, washed with water, brine, dried over Na2SO4, filtered, concentrated, and purified by HPLC to afford a light yellow solid as 2R,3S)-3-([1,2,4]triazolo[4,3-a]pyrazin-8-ylamino)-1-((R)-6-bromo-2,2-spirocyclobutanechroman-4-ylamino)-4-phenylbutan-2-ol. MS m/z: 551.1 (M+1).

According to the analysis of related databases, 68774-77-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Amgen Inc.; US2010/120774; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 68774-77-6, name is 8-Chloro[1,2,4]triazolo[4,3-a]pyrazine, molecular formula is C5H3ClN4, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Application In Synthesis of 8-Chloro[1,2,4]triazolo[4,3-a]pyrazine

A stirred mixture of (-)-R-tert-butyl 4-(aminomethyl)-3,3-difluoropiperidine-1-carboxylate (230mg, 0.92 mmol), 8-chloro-[1,2,4]triazolo[4,3-a]pyrazine (127 mg, 0.83 mmol) and DIPEA (0.30 mL, 1.8 mmol) in n-BuOH (5 mL) was heated to 95C under nitrogen for 13 hr. The reaction mixture was allowed to cool to room temperature and concentrated in vacuo. The residue was purified by column chromatography over silica gel (ethyl acetate/hexane = 1/1) to afford the title compound as a white powder (210 mg, 62%). MS (ESI) calcd for C16H22F2N602: 368.2; found: 369.1 [M+H]. 1H NMR (400 MHz, CDCI3) 6 8.72 (s, 1H), 7.41 (d, J = 4.8 Hz, 1H), 7.35 (d, J = 4.8 Hz, 1H), 6.50-6.45 (m, 1H), 4.47-4.09 (m, 2H), 4.02-3.96 (m, 1H), 3.79-3.72 (m, 1H), 3.09-2.69 (m, 2H), 2.45-2.29 (m, 1H), 1.92-1.87 (m, 1H), 1.68-1.58 (m, 1H), 1.47 (s, 9H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 68774-77-6, its application will become more common.

Reference:
Patent; RUGEN HOLDINGS (CAYMAN) LIMITED; SHAPIRO, Gideon; (246 pag.)WO2016/196513; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 68774-77-6, A common heterocyclic compound, 68774-77-6, name is 8-Chloro[1,2,4]triazolo[4,3-a]pyrazine, molecular formula is C5H3ClN4, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a solution of the product of Example 365A (70 mg, 0.153 mmol) in N,N- dimethylformamide (1 mL) was added 8-chloro-[l,2,4]triazolo[4,3-a]pyrazine (35.5 mg, 0.230 mmol) and N,N-diisopropylethylamine (0.080 mL, 0.460 mmol). The reaction mixture was stirred for 4 days at 70 C and then was purified by preparative HPLC [Waters XBridge CI 8 5 mupiiota OBD column, 30 x 100 mm, flow rate 40 mL/minute, 5-100% gradient of acetonitrile in buffer (0.1 % trifluoroacetic acid)] to give the title compound (15 mg, 0.026 mmol, 17% yield). JH NMR (400 MHz, DMSO-<) delta ppm 9.17 (s, IH), 7.75 (d, J = 4.8 Hz, IH), 7.54 (s, IH), 7.45 (t, J = 8.9 Hz, IH), 7.23 (d, J = 4.9 Hz, IH), 7.00 (dd, J = 11.4, 2.9 Hz, 2H), 6.79 (ddd, J = 9.0, 2.9, 1.2 Hz, IH), 4.42 (s, 2H), 4.17 - 4.14 (m, 2H), 2.64 - 2.50 (m, IH), 2.35 (ddd, J = 12.8, 9.4, 2.9 Hz, IH), 2.27 - 2.13 (m, IH), 2.04 - 1.77 (m, 8H); 19F NMR (376 MHz, DMSO-<) delta ppm - 75.00, -114.17; MS (ESI+) m/z 461 (M+H)+ . The synthetic route of 68774-77-6 has been constantly updated, and we look forward to future research findings. Reference:
Patent; CALICO LIFE SCIENCES LLC; ABBVIE INC.; MARTIN, Kathleen, Ann; SIDRAUSKI, Carmela; FROST, Jennifer, M.; PLIUSHCHEV, Marina, A.; TONG, Yunsong; BLACK, Lawrence, A.; XU, Xiangdong; SHI, Lei; ZHANG, Qingwei, I.; CHUNG, Seungwon; SWEIS, Ramzi, Farah; DART, Michael, J.; RANDOLPH, John, T.; MURAUSKI, Kathleen; (674 pag.)WO2019/90076; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 68774-77-6, name is 8-Chloro[1,2,4]triazolo[4,3-a]pyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. category: Pyrazines

[0538] To a mixture of (R)-5-(2-(4-aminopiperidin-1-yl)-1-hydroxyethyl)-4-methylisobenzofuran-1(3H)-one hydrochloride(60 mg, 0.16 mmol) and 5-cyano-2-fluoropyridine (20 mg, 0.16 mmol) in N-methylpyrolidinone (550 ml) was addedDIEA (57 ml, 0.33 mmol) in a microwave tube at room temperature. The tube was sealed and heated at 100C for 4 h.The mixture was cooled and partitioned between EtOAc/hexanes (2:1) and water. The aqueous layer was extractedwith EtOAc (2x). The combined organic phase was washed with brine, dried (MgSO4), filtered and concentrated. Theresulting residue was purified by prep TLC (silica gel, 10% MeOH/DCM) to provide (R)-6-(1-(2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)ethyl)piperidin-4-ylamino)nicotinonitrile. 1H-NMR (CDCl3, 500 MHz), delta 8.39 (m, 1H),7.82 (s, 2H), 7.60 (m, 1H), 6.41 (m, 1H), 5.29 (s, 2H), 4.92 (m, 1H), 3.23 (m, 1H), 2.96 (m, 1H), 2.39-2.46 (m, 4H), 2.18(s, 3H), 2.02 (m, 4H); LC-MS (IE, m/z): 393 [M + 1]+:_[0542] 5-((1R)-2-(6-([1,2,4]Triazolo[4,3-a]pyrazin-8-ylamino)-3-azabicyclo[3.1.0]hexan-3-yl)-1-hydroxyethyl)-4-methylisobenzofuran-1(3H)-one was prepared in a similar fashion to that described for the synthesis of EXAMPLE 111 startingfrom 5-((1R)-2-(6-Amino-3-azabicyclo[3.1.0]hexan-3-yl)-1-hydroxyethyl)-4-methylisobenzofuran-1(3H)-one hydrochlorideand 8-chloro-[1,2,4]triazolo[4,3-a]pyrazine. _LC-MS (IE, m/z): 407 [M + 1]+.

The synthetic route of 68774-77-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck Sharp & Dohme Corp.; WALSH, Shawn; PASTERNAK, Alexander; CATO, Brian; FINKE, Paul, E.; FRIE, Jessica; FU, Qinghong; KIM, Dooseop; PIO, Barbara; SHAHRIPOUR, Aurash; SHI, Zhi-Cai; TANG, Haifeng; (136 pag.)EP2755656; (2016); B1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 68774-77-6, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 68774-77-6, name is 8-Chloro[1,2,4]triazolo[4,3-a]pyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 1.28. (3 ?,4S)-4-methylbenzyl 4-(([l,2,4]triazolo[4,3-a]pyrazin-8-ylamino)methyl)-3- fluoropiperidine-l-carboxylate (E2-1.2). [0265] A mixture of 8-chloro-[l,2,4]triazolo[4,3-a]pyrazine (120 mg, 0.78 mmol), (3R,4S)-4- methylbenzyl 4-(aminomethyl)-3-fluoropiperidine-l-carboxylate hydrochloride (297 mg, 0.94 mmol) and DIPEA (0.65 mL, 3.9 mmol) in n-BuOH (4 mL) was heated to 120C under N2 atmosphere. After stirring overnight at 120C, the mixture was cooled down to room temperature and concentrated under vacuum. The concentrate was partitioned into EtOAc and water. The organic phase was washed with water, brine, dried over Na2S04 and concentrated. The concentrate was purified by column chromatography over silica gel (eluent: 100% ethyl acetate) to afford the title compound as a brown powder (187 mg, 78%). MS (ESI) calcd for C20H23FN6O2: 398.2; found: 399.3[M+H]. *H NMR (400 MHz, CD3OD) delta 9.09 (s, 1H), 7.69 (d, J = 4.8 Hz, 1H), 7.30 (d, J = 4.8 Hz, 1H), 7.24 (d, J = 8.0 Hz, 2H), 7.16 (d, J = 8.0 Hz, 2H), 5.08 (s, 2H), 4.85-4.71 (m, 1H), 4.50-4.40 (m, 1H), 4.28-4.20 (m, 1H), 3.68-3.63 (m, 1H), 3.60-3.55 (m, 1H), 3.11-3.00 (m, 1H), 2.95-2.80 (m, 1H), 2.33 (s, 3H), 2.30-2.11 (m, 1H), 1.71-1.57 (m, 2H).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 8-Chloro[1,2,4]triazolo[4,3-a]pyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; RUGEN HOLDINGS (CAYMAN) LIMITED; SHAPIRO, Gideon; (239 pag.)WO2016/100349; (2016); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem